7900. Protoverine

Nomenclature

CAS number: 76-45-9
(3β,4α,6α,7α,15α,16β)-4,9-Epoxycevane-3,4,6,7,14,15,16,20-octol.
C27H43NO9; mol wt 525.63.
C 61.70%, H 8.25%, N 2.66%, O 27.39%.

Description and references

Obtained by alkaline hydrolysis of protoveratrine A: Poethke, Arch. Pharm. 275, 571 (1937); Stoll, Seebeck, Helv. Chim. Acta 36, 718 (1953). Structure: Kupchan et al., Chem. Ind. (London) 1958, 1626; J. Am. Chem. Soc. 81, 1009 (1959); 82, 2242 (1960). Comparative toxicity: O. Krayer et al., J. Pharmacol. Exp. Ther. 82, 167 (1944); K. Tanaka, ibid. 113, 89 (1955).

Chemical structure

Properties

Fine needles from methanol, dec 220-222°. [α]D20 -15.7° (c = 1.1 in pyridine). Sol in CHCl3, methanol, pyridine. LD50 i.v. in mice: 194.0 mg/kg (Krayer). LD50 s.c. in male mice: 520 mg/kg (Tanaka).